Startup Life : The Depression of Success

It was Thursday, September 25, 2014 in Dallas, Texas. Following a successful lunch meeting, I shook hands with a very notable Chicago attorney who was now my new business partner. On the 4 hour drive home that evening, I was on an emotional high.

The Rededication

It was just 6 months prior that I had decided to make a pivot in my career and re-introduce software application development into my life. What’s true about coding is that is not like quite like riding a bike. The moment you’re out of practice is the moment you forget how to pedal. Although I studied coding in college, it had been close to 7 years since I had developed an app. To get reacquainted I taught myself PHP via w3schools.com. The reason for doing so was after years spent in real estate, I had identified an opportunity to provide Real Estate Attorneys with a suite of software applications that would enhance firm productivity, organization, and profitability.

In the early beginnings of this new Startup, I worked from the home where I grew-up in St. Louis. Many long days of coding in addition to other tasks that come with the territory of being involved in a Startup. I was not only the lead of software, I was also over graphic design, client care, sales, marketing, advertising, etc. Basically, you don’t ‘not’ do something needed because there isn’t the staff support, you make it happen by any means necessary. In the early stages of most companies, it’s common to wear multiple hats.

During the first year, the company was progressing slower than anticipated. To give it more of myself, I moved to Chicago. This was beneficial as there is just no substitute for having boots-on-the-ground where you’re doing business. A valuable lesson learned from my earlier days flipping houses.

Zero to 100 Real Quick

By the start of year two, we went from under-performing to over-performing within a small time span. We had a huge spike in growth. This was both good and bad at the same time. The good was that our Startup was beginning to find its way within the marketplace, focusing on the underserved market niches brought us the growth.

The bad was that my workload increased substantially. We outgrew our internal infrastructure within a small period of time. This meant, I personally became one of many process bottlenecks.

My workload increase was so substantial that even by putting in 70-80 hour work weeks, I was just barely meeting deadlines. My life began to become a repetitive cycle of eat, sleep, work, drink. And to be specific, I wasn’t eating the best foods. I was going after the comfort foods vs. the whole foods, my quality of sleep was poor as most nights I was stressed out, my work accuracy was suffering as I was more mistake-prone due to higher load, and to calm all of my anxieties of failure was a hard drink (or two) as the medicine nearly every night.

Entrepreneurship isn’t Sexy

Shit got so bad, I started to even question my own sanity on a weekly basis. “WTF did I sign up for?” I felt cursed and trapped by my own ambition. I asked myself other questions like, “exactly why do you feel like you’re too good to have a regular job?” As at least those people had their weekends. All jobs couldn’t be that bad, especially those with companies that pride themselves on corporate culture and being staffed with innovative minds. Maybe I just never focused hard enough on finding the right company to work for.

After receiving this email out-of-the-blue, I took this call with Google. Primarily, just because it was “Google”. On the call I was reminded that there was no way I was going back to the corporate world. Even for Google. I was just going through a slump. All sluggers have a slump. I wasn’t crazy enough to jump ship.

There was financial strain which didn’t help my cause. Because I was involved with a company in its early stages, we weren’t making enough money yet for me to draw a salary. I had to rely on the small amount of passive income I made online and other small hustles from time to time. What was most frustrating was that I was turning down side projects presented to me because I just didn’t have the time bandwidth to handle anything more.

20 grand.

I turned down a project for 20 grand while my personal bank account had merely 3 figures.

I even had the audacity to think that a girlfriend would work out. It was a long-distance romance so I thought perhaps that would actually be a favorable factor, given my work load. Long-distance relationships don’t require much time, right? After trying to make it work with the Skype sessions and the sporadic in-person visits, it took me a few months to realize that I just plain wasn’t emotionally available. And that wasn’t fair to her or myself. I wasn’t emotionally available because I didn’t have anytime for myself. I wasn’t happy alone, so how could I be happy with her? I gradually became more distant towards her. For instance, we would be out to eat and I would habitually space out and mentally turn the volume down on her voice and drift away in my own thoughts like, “did I double check those documents?” I’d sneak looks at my phone in anticipation of emails. I was empty on the inside. So to be fair, I broke it off. In the short-term I was actually happy about the extra time I was getting back to myself. But over the long-term, I grew more sad. My heart was broken because I knew I had broke her heart.

Don’t mistake this for a pity party

This is merely one entrepreneurs’ synopsis of where he’s been for the last 2 years. I took a break from blogging, from travel, from healthy eating, and all of the other things that brought me happiness to bootstrap a startup. In hindsight, this was a mistake. No matter what your endeavor, don’t lose sight of what makes you happy. For sure, don’t stop doing those things even if time constraints dictate that you must do less of them.

Life is all about balance.

When my life became unbalanced, it became very unpleasant. I hated the start of every day. During the worst of it all, I was depressed. It took quite an effort to come out of that funk. Lots of prayer, meditation, and a rededication to health and fitness.

On top of that, our company has grown exponentially over the last quarter and has much better systems in place to handle load. This and new staff members round out a company poised for more greatness which I’m really excited about.

2016 was one of the roughest years of my life

For the final 60 days of last year, I couldn’t help but to anxiously anticipate 2017’s arrival just so I could mention 2016 with a past tense. Lay it to rest. I’m stronger and wiser because of such a trying year. Never again will I sacrifice my health and well being for the prosperity of any company. It’s not worth it. Never again will I turn to alcohol or any other drug to satiate my anxiety. Never again will I poorly prioritize my own personal happiness. And neither should you.

Be well my friends.

Happy New Year!

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Why I Do This

These days most of my hours are spent in solitude. Entrepreneurial demands consume the extreme majority of my time. However, every now and again, I feel the responsibility to pay-forward by sharing resources and experiences concerning health (Get Fit), entrepreneurship (Get Money), travel (Globe Trot), and philanthropy (Give Back) with a reader such as yourself.

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